A natural like O-glycoconjugate polycyclic compound 4 was obtained by a multistep procedure starting from N-(3-methyl-1-(4-nitrophenyl)-1H-pyrazol-5-yl)acetamide. The glycosyl derivative 4 showed antiproliferative activity against all the tumoral cell lines of the NCI panel in the range 0.47–5.43 μM. Cytofluorimetric analysis performed on MDA-MB231, a very aggressive breast cancer cell line, which does not express estrogen, progesterone and HER-2/neu receptors, showed that 4 is able to induce prolonged cell cycle arrest at G2/M phase and morphological signs of differentiation. These events are correlated with down-regulation of both cyclin B1 and cdc2, the cyclins involved in G2/M transition, as well as up-regulation of cyclin-dependent kinase (CDK) inhibitor p21 Cip1/Waf1.

Maggio, B., Raimondi, M., Raffa, D., Plescia, F., Scherrmann, M., Prosa, N., et al. (2016). Synthesis and antiproliferative activity of a natural like glycoconjugate polycyclic compound. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 122, 247-256 [10.1016/j.ejmech.2016.06.027].

Synthesis and antiproliferative activity of a natural like glycoconjugate polycyclic compound

MAGGIO, Benedetta;RAIMONDI, Maria Valeria;RAFFA, Demetrio;PLESCIA, Fabiana;LAURICELLA, Marianna;D'ANNEO, Antonella;DAIDONE, Giuseppe
2016-01-01

Abstract

A natural like O-glycoconjugate polycyclic compound 4 was obtained by a multistep procedure starting from N-(3-methyl-1-(4-nitrophenyl)-1H-pyrazol-5-yl)acetamide. The glycosyl derivative 4 showed antiproliferative activity against all the tumoral cell lines of the NCI panel in the range 0.47–5.43 μM. Cytofluorimetric analysis performed on MDA-MB231, a very aggressive breast cancer cell line, which does not express estrogen, progesterone and HER-2/neu receptors, showed that 4 is able to induce prolonged cell cycle arrest at G2/M phase and morphological signs of differentiation. These events are correlated with down-regulation of both cyclin B1 and cdc2, the cyclins involved in G2/M transition, as well as up-regulation of cyclin-dependent kinase (CDK) inhibitor p21 Cip1/Waf1.
2016
Maggio, B., Raimondi, M., Raffa, D., Plescia, F., Scherrmann, M., Prosa, N., et al. (2016). Synthesis and antiproliferative activity of a natural like glycoconjugate polycyclic compound. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 122, 247-256 [10.1016/j.ejmech.2016.06.027].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/180516
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